401641-23-4

Upstream product

• 34930-11-5 S-(4-methylbenzyl)dithiocarbazate 
• 471-32-9 dithiocarbonic acid hydrazide 
• 104-82-5 4-Methylbenzyl chloride 

Relevant academic research and scientific papers

Isolation, characterization and X-ray structure determination of 2,5-bis(4-methylbenzylthio)-1,3,4-thiadiazole

The reaction of hydrazine hydrate with carbon disulfide and 4-methylbenzyl chloride in basic solution yielded 2,5-bis(4-methylbenzylthio)-1,3,4-thiadiazole (C18H18N2S3, compound 1) in addition to the expected S-4-methylbenzyldithiocarbazate. The molecule has approximate twofold symmetry with the C=S bond lying on the pseudo axis. The five membered ring is planar with the three S atoms mutually syn, and with pendent 4-methylbenzylthio substituents; the dihedral angle between the terminal rings is 52.21(7). The compound 1 crystallizes in the triclinic space group P 1 with a = 6.0139(3) A, b = 11.8694(7) A, c = 12.6330(7) A, α = 72.583(5), β = 82.827(4), γ = 89.882(4) and Z = 2. Graphical Abstract: In situ cyclization of an authenticated dithiocarbazate gave rise to a supramolecular layerered assembly of new molecules containing a 1,3,4-thiadiazole ring system having a strictly planar central core with mutually syn sulfur atoms and terminal aryl groups twisted out of this plane.[Figure not available: see fulltext.]

Synthesis of novel 2,5-bis(substituted thio)-1,3,4-thiadiazoles by acid catalyzed intermolecular cyclization reactions of substituted dithiocarbazates as a possible 2019-nCoV main protease inhibitor

A convenient and facile synthesis of a privileged pharmaceutical scaffolds, 2,5-bis(substituted thio)-1,3,4-thiadiazoles is accomplished. The reaction of hydrazine hydrate with carbon disulfide and substituted alkyl/aryl chloride in basic medium yielded S-substituted alkyl/aryl dithiocarbazates in high yield. These dithiocarbazates on reaction with tetrafluoro acetic acid underwent a unique acid catalyzed intermolecular cyclization reaction to afford a novel 2,5-bis(substituted thio)-1,3,4-thiadiazoles. A simple procedure and high yields are the characteristic features of these reactions. These compounds are characterized on the basis of physico-chemical and spectral (FT-IR, ESI Mass, 1H, 13C and DEPT 135° 13C {1H} NMR) studies. Compound 2b crystallizes in orthorhombic system with point group P bca. Using the DFT/B3LYP/6–311 G (d,p) level of theory, HOMO-LUMO energy gap and molecular electrostatic potential (MEP) analyses were carried out. The HOMO-LUMO energy gap allowed the calculation of chemical hardness, chemical inertness, electronegativity and the electrophilicity index of the molecule, which depicted their potential kinetic stability and reactivity. The molecular docking studies of 2b-2e with 2019-nCoV main protease(7BRO) revealed binding free energies of (ΔGb) = -6.22, -5.38, -4.43 and -4.25 kcal mol?1 respectively. Docking study revealed that the aromatic congeners exhibit appreciable therapeutic efficiency to be used as 2019-nCoV main protease inhibitors.